There's been good response to my earlier post (really, July?!?) about upgrading a client's server from SBS 2003 to SBS 2011 -- people want to know how the story ended. So, forgive me for taking so long to finish up. So, this will be short of details since I didn't take notes and am relying on memory.
TL;DR - Did a clean install. Recreated users, shares and printers. Export mailboxes to PSTs. Copied data over. Reimported mailboxes. Got on with my life.
For the second run at upgrading the server, I had a few new tools at my disposal.
First, was a virtual copy of their server. Since their server was already virtualized, I just stopped VMWare, made a copy of the VM and took it back to my office. I loaded it up on a little Vostro 200 I had laying around (the server was amazingly peppy, all things considered) and then figured I'd do 99% of the migration off-site and then drop the box in and copy what was left of the data and mailboxes over.
I made the smart move and took GHOST images of the new box at every juncture, so I could "easily" roll back. (Granted, the roll back takes 15 minutes, but it's waaaaay better than having to sit thru the unpacking of files every time something goes wrong.)
I will say it took an inordinate amount of time to get the right drivers to get the Dell T310 work with Sysinternals' ERD Commander 5.0 (Microsoft version; not the pre-buyout version with Firefox in it...) but it was worth it.
Let's say I rolled back more than a few times. Learning a little more each time; or sometimes just doing everything identically, but having it work the second time around.
This guide came in handy: http://blog.mpecsinc.ca/2009/06/sbs-2003-to-sbs-2008-migration-guide.html
After doing this dance for a couple days, it got to a point where I was fed up with the roadblocks and things not working right (like migrated uses not showing up in the users applet). From an email I sent to my partner at midnight the night before we were supposed to be on site, where I make the call to punt:
"OK, I've had it. Every time I think I got it, there's some fucking error somewhere. I assume its in the old box somewhere -- a remnant of the P2V or something. So, fuck the migration. Their environment isn't so hard that we can't just do a clean install from scratch, remake the 10 users and the 4 shares and just be done. Can you come down tomorrow since we're going to have join the machines to a new domain? I think the biggest challenge is going to be exporting/importing [the owner's] 8GB PST. I'll have all the users set up and the groups and most of the data copied over, so it'll just be joining the computers to the new domain and importing the mail."
From there, it was a dream -- everything worked just fine. We had one machine exporting people's PST files for later import.
(WARNING: You lose Single Instance Storage when you do it this way, so your Exchange store will be bigger than it was due to duplication of attachments, etc. This may not be right for you. YMMV.)
At about 1:30 AM we were ready to move the new server into the copy room where it was going to stay. The server asked to apply 59 updates, and like idiots, we let it, and that's where it all went to shit.
The reboot happened and then nothing but "Applying Updates, Stage 3 of 3..."
After an hour of staring at that screen, I sent my partner home. No sense have two of us stuck in graybar land.
After two hours, I started Googling solutions to the problem. Eventually I was able to start the server and get to safe mode where I could edit some XML files and cross my fingers and wait more.
After another hour, I just left. It was almost 4 in the morning by that point, so I got a room at a nearby motel (to save myself the 65 minute each way commute to the client office) and crashed hoping to get back onsite before everyone showed up at 8.
As I wrote in my post-mortem email to Brian at 11:20 AM:
Subject: What a fucking mess
Everything works and nothing works,
Ended up staying at the local Days Inn and crossed my fingers that the thing would roll back while I slept, and when I came back at 8:15, we were at CTRL+ALT+DEL so it seems to be OK,m tho it lists all 59 updates as pending. There's a possibility they'll never take. (Fun!)
"Where are my contacts!?!" (nickname) - bring them over and all the nicknames for the internal people are all wrong, so the mail bounces. NK2Edit to the rescue.
Scanner set up.
Abacus' DRM is driving me up a fucking wall.
Some documents that people were working on last night never made it over -- feels like there wasn't a sync done, and since we generally deleted the offline files from the workstations to eliminate the error we were getting at logoff sync... DOH. Happily, it seems they were able to recreate them with little effort, so it was an inconvenince, but not a show-stopper.
People don't like to use their address books, I find -- they really REALLY rely on their NK2 files -- so when doing any sort of migration, don't overlook them. NK2Edit is the greatest tool in the world.
I hate DRM. I think it only hurts legitimate users, pirates get past it with little effort, so it only serves to create issues for paid users at the worst possible times -- like when people need to use their time and billing systems and the support center isn't open for another hour or two...
The document sync issue wasn't something we thought was an issue -- we made sure offline files were all sync'd up, but users reported some documents didn't copy over, and I'm not sure what else to attribute it to.
In the time since we did this, the 59 updates did in fact take and the server didn't fall apart or fail.